The interaction of international counter-terrorism laws with IHL is an area of renewed focus, amid widespread concern that the former are being (mis)applied to criminalise the provision of humanitarian assistance envisaged under the latter. The Security Council has begun to consider this issue in resolutions adopted in March and July 2019, but difficult questions of law and fact remain. These questions have significant practical consequences – for humanitarian agencies and those they seek to assist, as well as for States that must weigh different, and possibly conflicting, legal obligations. Much of the analysis to date and the solutions proposed, pay insufficient attention to the specifics of each legal regime.